IP Library Granted Patent US 8,410,024
Granted Patent B2
US 8,410,024 · App. 13/040,413 · Granted Apr 2, 2013

Use of maleimide salts to control phytopathogenic fungi

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Quick Facts
Patent No.
US 8,410,024
App. No.
13/040,413
Granted
Apr 2, 2013
Kind
B2
Abstract

The present invention relates to the use of new and known maleimide salts for controlling phytopathogenic fungi, and also to methods for controlling phytopathogenic fungi in crop protection, in the household and hygiene sectors and in materials protection, and also to crop protection compositions comprising these maleimide salts.

Claims (59)

1. A method of controlling phytopathogenic fungi, comprising applying a composition containing at least one compound of formula (I)

in which

(a) Y 1 is the group of the formula (II)

Y 2 is the group of the formula (III)

m is 1, n is the ionic charge of X, and

X is an anion selected from Cl − or Br − ,

(b) Y 1 is the group of the formula (II)

Y 2 is —S − ,

and m is 0,

or (c) Y 1 is —S − ,

Y 2 is —S − ,

m is 1, n is the ionic charge of X, and

X is a cation selected from H + , Ag + , Co 2+ , Cu 2+ , Fe 2+ , Mn 2+ , Ni 2+ , Pd 2+ , Zn 2+ , and

R 1 is hydrogen; C 1 -C 8 -alkyl optionally substituted with one or more identical or different halogen, —OR 10 , or —COR 11 ; C 3 -C 7 -cycloalkyl or C 3 -C 7 -cyclo-alkyl-C 1 -C 2 -alkyl, each of which is optionally substituted with one or more identical or different halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl; or aryl, aryl-(C 1 -C 4 -alkyl), or arylsulphonylamino, each of which is optionally substituted in the aryl moiety with one or more identical or different halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, —COR 11 , or sulphonylamino,

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 independently of one another are hydrogen, C 1 -C 6 -alkyl, or phenyl or benzyl, each of which is optionally substituted with one or more identical or different halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylthio,

R 10 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, or aryl which is optionally substituted with one or more halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl, and

R 11 is hydroxyl, C 1 -C 4 -alkyl, or C 1 -C 4 -alkoxy

to the fungi, their habitat, or a combination thereof.

2. The method of claim 1 , wherein

R 1 hydrogen; C 1 -C 6 -alkyl optionally substituted with one or more identical or different fluorine, chlorine, bromine, —OR 10 , or —COR 11 ; C 3 -C 7 -cycloalkyl or C 3 -C 7 -cycloalkyl-C 1 -C 2 -alkyl, each of which is optionally substituted with one or more identical or different chlorine, methyl, or trifluoromethyl; or phenyl, phenyl-(C 1 -C 4 -alkyl), or phenylsulphonylamino, each of which is optionally substituted with one or more identical or different fluorine, chlorine, bromine, methyl, trifluoromethyl, —COR 11 , or sulphonylamino,

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 independently of one another are hydrogen, C 1 -C 4 -alkyl, phenyl, or benzyl,

R 10 is hydrogen, methyl, ethyl, methylcarbonyl, or ethylcarbonyl, or phenyl which is optionally substituted with one or more fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, or trifluoromethyl, and

R 11 is hydroxyl, methyl, ethyl, methoxy, or ethoxy;

with the proviso that

if X is an anion, then X is Cl − ; and

if X is a cation, then X is H + , Ag + , Fe 2+ , Mn 2+ , or Zn 2+ .

3. The method of claim 1 , wherein

R 1 is hydrogen; C 1 -C 5 -alkyl optionally substituted with one or more identical or different fluorine, chlorine, hydroxyl, methoxy, ethoxy, methylcarbonyloxy, or carboxyl; cyclopropylmethyl or C 3 -C 7 -cycloalkyl optionally substituted with one or more identical or different chlorine, methyl, or trifluoromethyl; or phenyl, benzyl, 1-phenethyl, 2-phenethyl, or 2-methyl-2-phenethyl, each of which is optionally substituted with one to three identical or different fluorine, chlorine, bromine, methyl, trifluoromethyl, —COR 11 , or sulphonylamino,

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 independently of one another are hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl,

R 10 is hydrogen, methyl, methylcarbonyl, or phenyl, and

R 11 is hydroxyl or methoxy;

with the proviso that

if X is an anion, then X is Cl − ;

if X is a cation, then X is Ag + , Mn 2+ , or Zn 2+ .

4. The method of claim 1 , further comprising one or more extenders, surface-active substances, or a combination thereof.

5. A compound of formula (IV)

in which

R 1a is hydrogen; C 1 -C 8 -alkyl optionally substituted with one or more identical or different halogen, —OR 10a , or —COR 11a ; C 3 -C 7 -cycloalkyl or C 3 -C 7 -cyclo-alkyl-C 1 -C 2 -alkyl, each of which is optionally substituted with one or more identical or different halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl; or aryl, aryl-(C 1 -C 4 -alkyl), or arylsulphonylamino, each of which is optionally substituted in the aryl moiety with one or more identical or different halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, —COR 11a , or sulphonylamino,

R 2a , R 3a , R 4a , R 5a , R 6a , R 7a , R 8a , and R 9a independently of one another are hydrogen, C 1 -C 6 -alkyl, or phenyl or benzyl, each of which is optionally substituted with one or more identical or different halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylthio,

R 10a is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, or aryl which is optionally substituted with one or more halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl,

R 11a is hydroxyl, C 1 -C 4 -alkyl, or C 1 -C 4 -alkoxy,

m is 1, n is the ionic charge of X a , and

X a is an anion selected from Cl − or Br − ,

with the proviso that if R 1a is hydrogen, methyl, hydroxymethyl, methylcarbonyloxymethyl, chloromethyl, benzyl, phenyl, or methoxymethyl and X a is Cl − , then R 2a , R 3a , R 4a , and R 5a are not all simultaneously hydrogen.

6. A compound of formula (V)

in which

R 1b is hydrogen; C 1 -C 8 -alkyl optionally substituted with one or more identical or different halogen, —OR 10b or —COR 11b ; C 3 -C 7 -cycloalkyl or C 3 -C 7 -cycloalkyl-C 1 -C 2 -alkyl, each of which is optionally substituted with one or more identical or different halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl; or aryl, aryl-(C 1 -C 4 -alkyl), or arylsulphonylamino, each of which is optionally substituted in the aryl moiety with one or more identical or different halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, —COR 11b , or sulphonylamino,

R 2b , R 3b , R 4b , and R 5b independently of one another are hydrogen, C 1 -C 6 -alkyl, or phenyl or benzyl, each of which is optionally substituted with one or more identical or different halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylthio,

R 10b is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, or aryl which is optionally substituted with one or more halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl, and

R 11b is hydroxyl, C 1 -C 4 -alkyl, or C 1 -C 4 -alkoxy,

with the proviso that if R 1b is hydrogen, methyl, hydroxymethyl, methylcarbonyloxymethyl, chloromethyl, benzyl, phenyl, or methoxymethyl, then R 2b , R 3b , R 4b , and R 5b are not all simultaneously hydrogen.

7. A compound of formula (VI)

in which

R 11c is hydrogen; C 1 -C 8 -alkyl optionally substituted with one or more identical or different halogen, —OR 10c , or —COR 11c ; C 3 -C 7 -cycloalkyl or C 3 -C 7 -cycloalkyl-C 1 -C 2 -alkyl, each of which is optionally substituted with one or more identical or different halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl; or aryl, aryl-(C 1 -C 4 -alkyl), or arylsulphonylamino, each of which is optionally substituted in the aryl moiety with one or more identical or different halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, —COR 11c , or sulphonylamino,

R 10c is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, or aryl which is optionally substituted with one or more halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl,

R 11c is hydroxyl, C 1 -C 4 -alkyl, or C 1 -C 4 -alkoxy,

m is 1, n is the ionic charge of X c , and

X c is a cation selected from Ag + , Co 2+ , Fe 2+ , Mn 2+ , Ni 2+ , Pd 2+ and Zn 2+ ,

with the proviso that if R 1c is hydrogen, methyl, hydroxymethyl, methylcarbonyloxymethyl, chloromethyl, benzyl, phenyl, or methoxymethyl, then X c is not Ag + .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 27, 2015
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 035051/0325 →